Electrochemical synthesis of sulfonamides in a graphite powder macroelectrode

Vicente, Dmistocles A.; Galdino, Danilo; Navarro, Marcelo; Menezes, Paulo H.

doi:10.1039/d0gc01360a

Cited by 14 publications

(5 citation statements)

References 29 publications

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“…For the preparation of sulfonamide compounds of type 1 and 2 (Figure 3), several procedures are present in the literature [54][55][56][57][58][59][60][61], and a few of them were also proposed recently in light of using more environmentally friendly green chemistry approaches [62][63][64][65][66].…”

Section: Synthesismentioning

confidence: 99%

In Silico Design, Synthesis, and Biological Evaluation of Anticancer Arylsulfonamide Endowed with Anti-Telomerase Activity

et al. 2022

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Telomerase, a reverse transcriptase enzyme involved in DNA synthesis, has a tangible role in tumor progression. Several studies have evidenced telomerase as a promising target for developing cancer therapeutics. The main reason is due to the overexpression of telomerase in cancer cells (85–90%) compared with normal cells where it is almost unexpressed. In this paper, we used a structure-based approach to design potential inhibitors of the telomerase active site. The MYSHAPE (Molecular dYnamics SHared PharmacophorE) approach and docking were used to screen an in-house library of 126 arylsulfonamide derivatives. Promising compounds were synthesized using classical and green methods. Compound 2C revealed an interesting IC50 (33 ± 4 µM) against the K-562 cell line compared with the known telomerase inhibitor BIBR1532 IC50 (208 ± 11 µM) with an SI ~10 compared to the BALB/3-T3 cell line. A 100 ns MD simulation of 2C in the telomerase active site evidenced Phe494 as the key residue as well as in BIBR1532. Each moiety of compound 2C was involved in key interactions with some residues of the active site: Arg557, Ile550, and Gly553. Compound 2C, as an arylsulfonamide derivative, is an interesting hit compound that deserves further investigation in terms of optimization of its structure to obtain more active telomerase inhibitors

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Section: Synthesismentioning

confidence: 99%

In Silico Design, Synthesis, and Biological Evaluation of Anticancer Arylsulfonamide Endowed with Anti-Telomerase Activity

et al. 2022

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“…A noteworthy discovery using graphite powder macroelectrodes for the electrochemical synthesis of sulfonamides 15 was made by Menezes and co‐workers in 2020 [46] . This development showed that the use of inexpensive sodium salts of sulfinic acid can produce sulfinyl radicals through electrochemical oxidation process.…”

Section: Electrochemical Synthesis Of Sufonamidesmentioning

confidence: 99%

Recent Advances in the Electrochemical Synthesis of Organosulfur Compounds

Amri

Wirth

2021

The Chemical Record

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Organosulfur compounds are being widely used in medicinal chemistry, as well as in organic transformations and in synthetic applications. Because of their interest in many areas, the development of sustainable and green synthetic methods to access various organosulfur compounds has a high influence on the chemistry community. Electroorganic synthesis has become a very valuable methodology for the synthesis of organosulfur compounds during the last decade. The use of electrochemical technology offers a green, sustainable and safe alternative to prepare and modify such compounds. This review summarises recent developments in the preparation of organosulfur compounds such as sulfoxides, sulfones, sulfinic esters, sulfonamides, thiosulfonates, sulfonyl fluorides and sulfoximines under electrochemical reaction conditions.

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“…30 However, these approaches have the disadvantage of the use of hazardous chemicals and solvents. Recently, the synthesis of sulfones based on electrochemical procedures for the sulfonylation of p -quinone methides 31 and amines 32 have also been reported.…”

Section: Introductionmentioning

confidence: 99%

Sulfonylation reactions photocatalyzed by quantum dots: rule of band-position and surface chemistry

Lima

Galdino

Sousa

et al. 2023

Catal. Sci. Technol.

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Electrochemical synthesis of sulfonamides in a graphite powder macroelectrode

Abstract: The electrochemical generation of sulfinyl radicals from commercially available and non-expensive sodium salts of sulfinic acids is described. Electrooxidation reactions were carried out in graphite powder macroelectrode using aqueous electrolyte...

Cited by 14 publications

References 29 publications

In Silico Design, Synthesis, and Biological Evaluation of Anticancer Arylsulfonamide Endowed with Anti-Telomerase Activity

In Silico Design, Synthesis, and Biological Evaluation of Anticancer Arylsulfonamide Endowed with Anti-Telomerase Activity

Recent Advances in the Electrochemical Synthesis of Organosulfur Compounds

Sulfonylation reactions photocatalyzed by quantum dots: rule of band-position and surface chemistry

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